Various mycaminosyl tylonolide derivatives have been known so far. However, mycaminosyl tylonolide derivatives are not known wherein an unsubstituted or substituted amino group, etc. is directly attached to the 14-position of the derivatives.
The compounds of this invention are novel compounds having excellent antibacterial activity, and have a characteristic in that the 14-position has a substituent selected from a hydroxyl group, a lower alkanoyloxy group, benzoyloxy group, azido group, or amino group which may optionally be substituted with a lower alkyl group or a lower alkanoyl group.
The subject matters of this invention are directed to such particular novel compounds, and the production methods for the compounds. The compounds also include the salts thereof such as acid addition salts.
1. (Technical Field)
This invention relates to macro-lactone compounds having a broad spectrum of antibacterial activity against Gram-positive and -negative bacteria. More particularly, it relates to new 14-substituted mycaminosyl tylonolide derivatives represented by the following general formula (I) ##STR3## (wherein R.sup.1 denotes hydroxyl group, a lower alkanoyloxy group, benzoyloxy group, azide group, or amino group which may optionally be substituted with an lower alkyl or a lower alkanoyl radical; R.sup.2 stands for hydrogen atom or hydroxyl group; R.sup.3 express hydrogen atom or formyl group; and means a double bond or a radical represented by ##STR4## and salts thereof.
2. (Description of the Prior Art)
A large number of patents have been filed on mycaminosyl tylonolide derivatives. For example, U.S. Pat. No. 4,438,109 filed by the present inventors discloses a wide variety of compounds in which the 23-position carbon of the macro-lactone ring has substituent groups such as hydroxyl, alkanoyloxy radicals and arylcarbonyloxy radicals; and European Patent Application (Laid-open) No. 70,170 also filed by the present inventors discloses compounds in which substituent group at the 23-position carbon in the macro-lactone ring and hydroxyl, halogen atoms and radicals represented by ##STR5## (wherein R.sub.a is hydrogen atom or a lower alkyl which may optionally be substituted with hydroxyl group, and R.sub.b is hydrogen atom, aryl, aralkyl, or a lower alkyl, aryl or aralkyl which may optionally be substituted with hydroxyl group).
However, the compounds of this invention are distinctly different in structure from the compounds mentioned above; the compounds of this invention are new mycaminosyl tylonolide derivatives and salts thereof which have never been found in nature, are very difficult to synthesize, and are characterized in that hydroxyl group, a lower alkanoyloxy group, benzoyloxy group, azido group, or amino group which may optionally be substituted with a lower alkyl or a lower alkanoyl radical, is directly attached to the 14-position.
In addition, the compounds of this invention have a broad spectrum of antibacterial activity against Gram-positive and-negative bacteria as detailed below.